WO1998003208A1 - Medical pressure-sensitive adhesives with high permeability to water vapour and high adhesive force, and plasters provided therewith - Google Patents
Medical pressure-sensitive adhesives with high permeability to water vapour and high adhesive force, and plasters provided therewith Download PDFInfo
- Publication number
- WO1998003208A1 WO1998003208A1 PCT/EP1997/003392 EP9703392W WO9803208A1 WO 1998003208 A1 WO1998003208 A1 WO 1998003208A1 EP 9703392 W EP9703392 W EP 9703392W WO 9803208 A1 WO9803208 A1 WO 9803208A1
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- Prior art keywords
- sensitive adhesives
- medical
- pressure sensitive
- weight
- medical pressure
- Prior art date
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 37
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 18
- 239000000853 adhesive Substances 0.000 title claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 230000035699 permeability Effects 0.000 title claims abstract description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 16
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 229920005862 polyol Polymers 0.000 claims abstract description 5
- 150000003077 polyols Chemical class 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 238000004132 cross linking Methods 0.000 claims abstract description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229920001228 polyisocyanate Polymers 0.000 claims description 2
- 239000005056 polyisocyanate Substances 0.000 claims description 2
- 239000011505 plaster Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- -1 dimethylaminoethyl groups Chemical group 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 239000011888 foil Substances 0.000 claims 1
- 229920001480 hydrophilic copolymer Polymers 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000000123 paper Substances 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229940127554 medical product Drugs 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N Suberic acid Natural products OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- AOHAPDDBNAPPIN-UHFFFAOYSA-N myristicinic acid Natural products COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000010972 statistical evaluation Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HRGUSFBJBOKSML-UHFFFAOYSA-N 3',5'-di-O-methyltricetin Chemical compound COC1=C(O)C(OC)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 HRGUSFBJBOKSML-UHFFFAOYSA-N 0.000 description 1
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920003149 Eudragit® E 100 Polymers 0.000 description 1
- 208000008454 Hyperhidrosis Diseases 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- IDDMFNIRSJVBHE-UHFFFAOYSA-N Piscigenin Natural products COC1=C(O)C(OC)=CC(C=2C(C3=C(O)C=C(O)C=C3OC=2)=O)=C1 IDDMFNIRSJVBHE-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 1
- 230000037336 dry skin Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000013460 sweaty Diseases 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- BMCJATLPEJCACU-UHFFFAOYSA-N tricin Natural products COc1cc(OC)c(O)c(c1)C2=CC(=O)c3c(O)cc(O)cc3O2 BMCJATLPEJCACU-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/58—Adhesives
- A61L15/585—Mixtures of macromolecular compounds
Definitions
- the present invention relates in particular to medical pressure sensitive adhesives which, in addition to excellent adhesion, have a water vapor permeability (WDD) of at least 30,000 gm ⁇ 2 -24 h "1 (measured on a pressure sensitive adhesive film with a weight of 40 g / m 2 ), and their use for Production of pressure sensitive medical products, e.g. for emergency or sports medicine.
- WTD water vapor permeability
- EP 0 415 055 describes pressure sensitive adhesives with the water-soluble salt of an uncrosslinked copolymer of an amino group-containing monomer and at least one alkyl (meth) acrylate.
- the object of the present invention is therefore to provide medical pressure-sensitive adhesives which adhere excellently to dry, moist and wet skin and which do not show the disadvantages mentioned above, such as predrying the skin, cytotoxic constituents and adhesive residues when peeling off, and which due to their high WDD of at least 30,000 gm '2 -24 h "1 at 40 g / m s adhesive film weight are also suitable for a longer wearing period.
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- Health & Medical Sciences (AREA)
- Hematology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention concerns medical pressure-sensitive adhesives which can adhere to dry or wet skin. The adhesives are characterized by a mixture of: a) between 20 and 50 wt. % of a hydrophilic (meth)acrylate copolymer containing tertiary amino groups; b) between 20 and 50 wt. % of a hydrophobic (meth)acrylate copolymer containing carboxyl groups; c) between 10 and 40 wt. % of one or a plurality of mono or dicarboxylic acids; d) between 0 and 10 wt. % of a polyol; and e) between 0.02 and 0.5 wt. % of a cross-linking system which reacts with at least one copolymer. The total of components a) to e) amounts to 100 wt. %, and the permeability to water vapour is ≥ 30,000 g m?-2 24 h-1¿, measured on a 40 νm-thick pressure-sensitive adhesive film.
Description
Medizinische Haftklebstoffe mit hoher Wasserdampf- durchläεεigkeit und Klebkraft und damit versehene Pflaster Medical pressure sensitive adhesives with high water vapor permeability and adhesive strength and plasters provided with them
Gegenstand der Erfindung sind auf trockener und nasser Haut haftfähige medizinische Haftklebstoffe und damit versehene Pflaster.The invention relates to medical pressure sensitive adhesives which are adhesive on dry and wet skin and plasters provided therewith.
Die vorliegende Erfindung betrifft insbesondere medizinische Haftklebstoffe, die neben einer ausgezeichneten Haftung eine Wasserdampfdurchlassigkeit (WDD) von mindestens 30.000 gm~2-24 h"1 (gemessen an einem Haftklebstoffilm mit einem Gewicht von 40 g/m2 ) aufweisen, und ihre Verwendung zur Herstellung haftklebender Medicalprodukte, z.B. für die Notfall- oder für die Sportmedizin.The present invention relates in particular to medical pressure sensitive adhesives which, in addition to excellent adhesion, have a water vapor permeability (WDD) of at least 30,000 gm ~ 2 -24 h "1 (measured on a pressure sensitive adhesive film with a weight of 40 g / m 2 ), and their use for Production of pressure sensitive medical products, e.g. for emergency or sports medicine.
Als Haftklebstoffe werden hier solche Klebstoffe bezeichnet, die durch Druck auf dem jeweiligen Untergrund reversibel haften.In this case, pressure-sensitive adhesives are those adhesives which are reversibly adhered to the respective substrate by pressure.
Die Wasserdampfdurchlässigkeit ist diejenige Menge Wasser, die aus einem mit dem Substrat verschlossenen, auf dem Kopf stehenden und mit Wasser gefüllten Gefäß (inverted cup) bei einem Umgebungsklima von 0°C und 20% r.H. durch das zu messende Substrat pro Fläche und Zeit entweicht.The water vapor permeability is the amount of water that flows out of a container that is closed with the substrate, upside down and filled with water (inverted cup) at an ambient climate of 0 ° C and 20% r.H. escapes through the substrate to be measured per area and time.
Aus der DE-OS 44 16 928 sind naßhaftende Klebstoffe auf Acrylatcopoly erbasis bekannt. Weitere Bestandteile sind quartäre Ammoniumgruppen enthaltende Emulgatoren, Emulgatoren, die Polyoxyalkylene enthalten, Polyvinylcarbonsäure, klebrigmachende Harze und Vernetzer. Der Nachteil der Gemäß dieser DE-OS gefertigten Produkte ist einerseits, daß die Klebstoffe auf feuchter Haut nur dann gut kleben, wenn diese vor der Applikation getrocknet wird, andererseits darin, daß die quartäre Ammoniumgruppen enthaltenden Emulgatoren nicht mit dem Polymergerüst
vernetzt werden, so daß sie im feuchten Milieu herausgelöst werden können und cytotoxisch wirken. Im übrigen reicht die dort beschriebene Wasserdampfdurchlässigkeit von 30.000 gm"2-24 h"1, gemessen an einem Haftklebstoffilm mit einem Gewicht von 30 g/m2, in vielen Fällen noch nicht aus.From DE-OS 44 16 928 wet adhesives based on Acrylatcopoly are known. Other constituents are quaternary ammonium group-containing emulsifiers, emulsifiers which contain polyoxyalkylenes, polyvinyl carboxylic acid, tackifying resins and crosslinking agents. The disadvantage of the products manufactured in accordance with this DE-OS is, on the one hand, that the adhesives only adhere well to damp skin if it is dried before application, and, on the other hand, that the emulsifiers containing quaternary ammonium groups do not have the polymer structure are crosslinked so that they can be extracted in a moist environment and have a cytotoxic effect. Otherwise, the water vapor permeability described there of 30,000 gm "2 -24 h " 1 , measured on a pressure-sensitive adhesive film with a weight of 30 g / m 2 , is still not sufficient in many cases.
Die EP 0 415 055 beschreibt Haftkleber mit dem wasserlöslichen Salz eines unvernetzten Copolymers aus einem aminogrupperihaltigen Monomer und mindestens einem Alkyl (meth) acrylat .EP 0 415 055 describes pressure sensitive adhesives with the water-soluble salt of an uncrosslinked copolymer of an amino group-containing monomer and at least one alkyl (meth) acrylate.
Der Nachteil dieses Klebers besteht einerseits darin, daß die klebenden Eigenschaften des so gefertigten Haftklebstoffs sehr stark von dem Restfeuchtegehalt abhängig sind, was aufwendige Steuerungen der Trocknungsbedingungen erforderlich macht, andererseits darin, daß der Klebstoff nach längerer Tragedauer soviel Feuchtigkeit absorbiert hat, daß der Klebstoff beim Abziehen des Trägermaterials vollständig auf der Haut bleibt und mühsam mit Seifenlauge entfernt werden muß.The disadvantage of this adhesive is, on the one hand, that the adhesive properties of the pressure-sensitive adhesive produced in this way are very heavily dependent on the residual moisture content, which requires complex control of the drying conditions, and, on the other hand, that after a longer period of use, the adhesive has absorbed so much moisture that the adhesive does not Peeling off the backing material remains completely on the skin and must be laboriously removed with soapy water.
Die Aufgabe der vorliegenden Erfindung ist daher die Bereitstellung medizinischer Haftklebstoffe, die auf trockener, feuchter und nasser Haut ausgezeichnet haften und dabei die oben erwähnten Nachteile wie Vortrocknung der Haut, cytotoxische Bestandteile und Klebstoffrückstände beim Abziehen nicht zeigen und die durch ihre hohe WDD von mindestens 30.000 gm'2-24 h"1 bei 40 g/ms Klebstoffilmgewicht auch für eine längere Tragedauer geeignet sind.The object of the present invention is therefore to provide medical pressure-sensitive adhesives which adhere excellently to dry, moist and wet skin and which do not show the disadvantages mentioned above, such as predrying the skin, cytotoxic constituents and adhesive residues when peeling off, and which due to their high WDD of at least 30,000 gm '2 -24 h "1 at 40 g / m s adhesive film weight are also suitable for a longer wearing period.
Diese überraschend guten Eigenschaften werden bei dem erfindungsgemäßen Haftklebstoff erreicht, der gekennzeichnet ist durch eine Mischung von a) 20- 50 Gew.-% eines hydrophilen, tertiäre A inogruppen enthaltende (Meth-)Acrylatcopolymerisa s, b) 20- 50 Gew.-% eines hydrophoben, carboxylgruppenhaltigen (Meth-)Acrylatcopoly erisats,
c) 10- 40 Gew.-% einer oder mehrerer Mono- oder Di-Carbonsäuren, d) 0 - 10 Gew.-% eines Polyols, e) 0,02 - 0,5 Gew.-% eines mit mindestens einem Copolymerisat reagierenden VernetzungsSystems, bei der die Summe der Komponenten a bis e 100 Gew.-Ss beträgt, mit einer Wasserdampfdurchlassigkeit von ≥ 30.000 gm"J-24 h"1, gemessen an einem 40 μm dicken Haftklebstoffilm.These surprisingly good properties are achieved in the pressure-sensitive adhesive according to the invention, which is characterized by a mixture of a) 20-50% by weight of a hydrophilic, tertiary amino groups-containing (meth) acrylate copolymer, b) 20-50% by weight. a hydrophobic, carboxyl group-containing (meth) acrylate copolymer, c) 10-40% by weight of one or more mono- or di-carboxylic acids, d) 0-10% by weight of a polyol, e) 0.02-0.5% by weight of one reacting with at least one copolymer Crosslinking system, in which the sum of components a to e is 100 parts by weight, with a water vapor permeability of ≥ 30,000 gm "J -24 h " 1 , measured on a 40 μm thick pressure-sensitive adhesive film.
Der erfindungsgemäße Haftklebstoff haftet sowohl auf trockener als auch auf schweißnasser Haut ausgezeichnet, er läßt sich rückstandsfrei von der Haut entfernen und hat eine so hohe WDD, daß er auch eine längere Tragedauer im feuchten Milieu ermöglicht.The pressure sensitive adhesive according to the invention adheres excellently to both dry and sweaty skin, it can be removed from the skin without residues and has a WDD so high that it also enables a longer wearing period in a moist environment.
Ein hydrophiles, tertiäre Aminogruppen enthaltendes Methacrylatcopolymerisat ist zum Beispiel Eudragit® E 100 der Fa . ROHM Pharma .A hydrophilic, tertiary amino group-containing methacrylate copolymer is, for example, Eudragit® E 100 from ROHM Pharma.
Durotak ® 1050 (Fa. National Starch & Chemical) stellt einDurotak ® 1050 (National Starch & Chemical) adjusts
Beispiel für ein hydrophobes, Carboxylgruppen enthaltendes Acrylatcopolymer dar .Example of a hydrophobic, carboxyl group-containing acrylate copolymer.
Als Carbonsäuren sind aurin-, Myriεtin- oder Palmitinsäure oder als Dicarbonsäuren Adipin-, Kork- oder Sebacinsäure zu nenne .Auric, myristic or palmitic acid or adipic, cork or sebacic acid as dicarboxylic acids are mentioned as carboxylic acids.
Glycerin ist ein erfindungεgemäßes Polyol .Glycerin is a polyol according to the invention.
Zur Gruppe der Vernetzter zählen Metallchelate, Metallsäureester, Polyisocyanate, Epoxidharze, Aziridinharze und Trizinharze.The group of crosslinking agents includes metal chelates, metal acid esters, polyisocyanates, epoxy resins, aziridine resins and tricin resins.
Gegenstand der Erfindung ist auch die Verwendung der erfindungsgemäßen Haftklebεtoffe zur Herstellung von haftklebenden Medicalprodukten, z.B. für die Notfall-,
Intensiv- und Sportmedizin sowie für Occlusiwerbände, wie z.B. transdermale Systeme. Die Medicalprodukte εind bei Bedarf durch Wasserdampf, γ-Bestrahlung bzw. Begasung mit Ethylenoxid sterilisierbar.The invention also relates to the use of the pressure-sensitive adhesives according to the invention for the production of pressure-sensitive medical products, for example for emergency, Intensive care and sports medicine as well as for occlusive volumes, such as transdermal systems. If required, the medical products can be sterilized by steam, γ-radiation or gassing with ethylene oxide.
Die Beurteilung der so gewonnenen Haftklebstoffe erfolgte, beschichtet auf atmungsaktive PUR-Folien, durch physikalisch technische Prüfungen wie WDD (die Wasserdampfdurchlassigkeit des Haftklebstoffilms berechnet sich nach der FormelThe pressure-sensitive adhesives obtained in this way were assessed, coated on breathable PUR films, by physical and technical tests such as WDD (the water vapor permeability of the pressure-sensitive adhesive film is calculated using the formula
WDD g.«..β WDD _ PU_R - .F.il.m WDD ., . „ )WDD g. «.. β WDD _ PU_R - .F.il.m WDD.,. ")
und Prüfung der Klebkraft auf Stahlplatten gemäß AFERA 4001 sowie auf einem Hautmodell aus Polyurethan. Bei diesem Hautmodell wird im Mittel eine um ca. 2N/25mm höhere Klebkraft erzielt als dem Mittelwert der Prüfung auf menschlicher Haut entspricht. Dies gilt praktisch unabhängig davon, ob der Haftklebstoff auf einem Naturoder Synthesekautschuk, einem lösemittel- oder wasserbasierten Acrylatcopolymer oder einem Silikon basiert.and testing the adhesive strength on steel plates according to AFERA 4001 and on a skin model made of polyurethane. This skin model achieves an average adhesive strength that is approx. 2N / 25mm higher than the average value of the test on human skin. This applies practically irrespective of whether the pressure sensitive adhesive is based on a natural or synthetic rubber, a solvent- or water-based acrylate copolymer or a silicone.
Zusätzlich erfolgte die Prüfung der Muster auf der Haut von 20 Probanden nach einem festgelegten Bewertungsschema mittels statistischer Auswertung, indem Streifen mit 2,5 cm x 5 cm auf der unbehaarten Innenseite der Unterarme (trocken) und jeweils 3 cm x 3 cm große Stücke in die frisch gewaschenen und getrockneten (feucht) bzw. ungetrockneten (naß) Handinnenseite geklebt wurden. Neben der subjektiven Beurteilung der Klebkraft nach 1 h bzw. nach 24 Stunden waren weitere Beurteilungβkriterien die Hautverträglichkeit und schmerzfreies, rückstandsfreies Ablösen. Die statistische Auswertung dieser Prüfungen, wobei jeweils ein Standard auf 100 % gesetzt wurde, ergab, daß Produkte mit den erfindungsgemäßen Haftklebstoffen
problemlos auf trockener und nasser Haut haften, keine Hautirritationen hervorrufen und praktisch rückstandsfrei entfernbar sind.In addition, the samples on the skin of 20 test persons were tested according to a defined evaluation scheme by means of statistical evaluation, in which strips measuring 2.5 cm x 5 cm on the hairless inside of the forearms (dry) and pieces measuring 3 cm x 3 cm in each freshly washed and dried (damp) or undried (wet) hands were glued. In addition to the subjective assessment of the adhesive strength after 1 h and after 24 hours, other assessment criteria were skin tolerance and painless, residue-free peeling. The statistical evaluation of these tests, whereby a standard was set to 100%, showed that products with the pressure-sensitive adhesives according to the invention adhere easily to dry and wet skin, do not cause skin irritation and can be removed practically without residue.
Die vorliegende Erfindung wird hier anhand des folgenden Beispiels näher erläutert:The present invention is explained in more detail using the following example:
Beispiel 1:Example 1:
In einem 1 1-Reaktionsgefäß mit Rührer, Tropftrichter. Rückflußkühler und Gasanschlußstutzen werden 200 g Ethylacetat vorgelegt und auf 80 °C erwärmt. Innerhalb von 50 min. wird unter Rühren eine Monomermischung aus 80 g n- Butylacrylat, 80 g ADAME (Elf Atochem), 40 g Methacrylsäure und 0,5 g VAZO 64 (Du Pont) zugetropft. Nach weiteren 6 h und Abkühlung auf 60°C werden zu diesem Copolymerisat A 60 g Ethylacetat und 40 g Isopropanol zusammen mit 120 g Laurinεäure und 22 g Adipinsäure gegeben. Der homogenen Mischung werden nach Abkühlung auf Raumtemperatur 20 g Glycerin und 340 g eines Copolymerisats B, das wie oben beschrieben aus 200 g n-Butylacrylat, 275 g 2- Ethylhexylacrylat, 25 g Acrylsäure und 2,5 g VAZO 64 in 500 g Ethylacetat polymerisiert wurde, beigemiεcht. Zur Vernetzung werden zusätzlich 100 g einer 2,5%igen Aluminiumacetylacetonatlösung (AlAcA) zugesetzt.In a 1 liter reaction vessel with stirrer, dropping funnel. The reflux condenser and gas connecting piece are placed in 200 g of ethyl acetate and heated to 80.degree. Within 50 minutes a monomer mixture of 80 g of n-butyl acrylate, 80 g of ADAME (Elf Atochem), 40 g of methacrylic acid and 0.5 g of VAZO 64 (Du Pont) is added dropwise with stirring. After a further 6 hours and cooling to 60 ° C., 60 g of ethyl acetate and 40 g of isopropanol are added to this copolymer A, together with 120 g of lauric acid and 22 g of adipic acid. After cooling to room temperature, the homogeneous mixture is polymerized with 20 g of glycerol and 340 g of a copolymer B which, as described above, is polymerized from 200 g of n-butyl acrylate, 275 g of 2-ethylhexyl acrylate, 25 g of acrylic acid and 2.5 g of VAZO 64 in 500 g of ethyl acetate was added. For crosslinking, an additional 100 g of a 2.5% aluminum acetylacetonate solution (AlAcA) are added.
Der so erhaltene Haftklebεtoff wird mittels einer Streichrakel in unterschiedlichen Schichtdicken auf eine silikonisierte Polyesterfolie beschichtet und bei 80°C 30 min. in einem Ablufttrockenschrank zu Haftklebefilmen mit einer Dicke von 25 μ , 45 μm und 60 μm (mit a, b, und c bezeichnet) getrocknet. Die Haftklebefilme werden auf eine 25 μm dicke Polyurethanfolie, die eine WDD von 40.000 g-m"2-24h"1 besitzt, transferkaεchiert . Die Ausprüfung (siehe Tabelle 1) erfolgte im Vergleich zu einem kommerziellen Standardprodukt, zusammengesetzt aus einem
30 μm dicken Haf klebstoffilm und einer 25 μm dicken PUR- Folie . Tabelle 1:The pressure-sensitive adhesive thus obtained is coated on a siliconized polyester film in different layer thicknesses by means of a doctor blade and at 30 ° C. for 30 minutes. dried in an exhaust air drying cabinet to form pressure-sensitive adhesive films with a thickness of 25 μm, 45 μm and 60 μm (denoted by a, b, and c). The pressure-sensitive adhesive films are transfer-coated onto a 25 μm-thick polyurethane film which has a WDD of 40,000 gm “2 -24h ” 1 . The test (see Table 1) was carried out in comparison to a commercial standard product, composed of one 30 μm thick adhesive film and a 25 μm thick P UR film. Table 1:
* 1 : sehr schwache oder gar keine Haftung* 1: very weak or no liability
Man erkennt beim Vergleich mit dem Standard ein annähernd gleiches Klebkraft-Niveau bei der Messung auf trockener Haut ( es herrschten normale Klimabedingungen) . Bei der Messung auf feuchter, besonders aber auf nasser Haut macht sich die Leistungskraft des neuen Haftklebstoffs bemerkbar. Während das Standardprodukt bei den meisten Testpersonen auf nasser Haut nicht mehr klebt, erzielt der erfindungsgemäße Haftklebstoff immer noch eine ausreichende Klebkraft .
A comparison of the standard shows an approximately the same level of adhesive strength when measuring on dry skin (normal climatic conditions prevailed). When measuring on damp, but especially on wet skin, the performance of the new pressure sensitive adhesive becomes noticeable. While the standard product no longer sticks to wet skin in most test subjects, the pressure-sensitive adhesive according to the invention still achieves sufficient tack.
Beispiel 2- 5:Example 2- 5:
Analog Beispiel 1 wurden folgende Mischungen verarbeitet (die Angaben beziehen sich jeweils auf den Feststoff) und BO ausgestrichen, daß ein Haftklebstoffilm der angegebenen Dicke entstand: A nalog Example 1, the following mixtures were processed (the data relate in each case to the solid) and BO was spread out so that a pressure-sensitive adhesive film of the indicated thickness was formed:
Die analoge Prüfung ergab folgende Werte:The analog test gave the following values:
Claims
1. Auf trockener und nasser Haut haftfähige medizinische Haftklebstoffe, gekennzeichnet durch eine Mischung von a) 20- 50 Gew.-% eines hydrophilen, tertiäre Aminogruppen enthaltenden(Meth- )Acrylatcopolymerisats, b) 20- 50 Gew.-% eines hydrophoben, carboxylgruppenhaltigen (Meth- )Acrylatcopolymerisats , c) 10- 40 Gew.-% einer oder mehrerer Mono- oder Di-Carbonsäuren, d) 0 - 10 Gew.-% eines Polyols, e) 0,02 - 0,5 Gew.-% eines mit mindestens einem Copolymerisat reagierenden Vernetzungssystems, bei der die Summe der Komponenten a bis e 100 Gew.-Ss beträgt, mit einer Wasserdampfdurchlässigkeit von > 30.000 gm"2-24 h"1, gemessen an einem 40 μm dicken Haftklebstoffilm.1. Medical pressure-sensitive adhesives which are adhesive on dry and wet skin, characterized by a mixture of a) 20-50% by weight of a hydrophilic, tertiary amino group-containing (meth) acrylate copolymer, b) 20-50% by weight of a hydrophobic, carboxyl group-containing (Meth) acrylate copolymer, c) 10-40% by weight of one or more mono- or di-carboxylic acids, d) 0-10% by weight of a polyol, e) 0.02-0.5% by weight a crosslinking system reacting with at least one copolymer, in which the sum of components a to e is 100 parts by weight, with a water vapor permeability of> 30,000 gm "2 -24 h " 1 , measured on a 40 μm thick pressure-sensitive adhesive film.
2. Medizinische Haftklebstoffe nach Anspruch 1, dadurch gekennzeichnet . daß das hydrophile Copolymer Dimethylaminoethylgruppen aufweist .2. Medical pressure sensitive adhesives according to claim 1, characterized. that the hydrophilic copolymer has dimethylaminoethyl groups.
3. Medizinische Haftklebstoffe nach Anspruch 1, dadurch qekennzeichnet . daß das hydrophobe Copolymer n- Butylacrylat-Monomereinheiten enthält .3. Medical pressure sensitive adhesives according to claim 1, characterized thereby. that the hydrophobic copolymer contains n-butyl acrylate monomer units.
4. Medizinische Haftklebstoffe nach Anspruch 1. dadurch gekennzeichnet , daß die Zahl der C-Atome in den organischen Säuren geradzahlig ist und bei 12-16 liegt.4. Medical pressure sensitive adhesives according to claim 1, characterized in that the number of carbon atoms in the organic acids is even and is 12-16.
5. Medizinische Haftklebstoffe nach Anspruch 1, dadurch gekennzeichnet , daß die Zahl der C-Atome in den organischen Dicarbonsäuren geradzahlig ist und bei 6-10 liegt.5. Medical pressure sensitive adhesives according to claim 1, characterized in that the number of carbon atoms in the organic dicarboxylic acids is an even number and is 6-10.
6. Medizinische Haftklebstoffe nach Anspruch 1, dadurch gekennzeichnet . daß das Vernetzungsmittel ein Metallchelat, ein Metallsäureester, ein verkapptes Polyisocyanat, ein Epoxid-, ein Aziridin- oder ein Triazinharz ist. 6. Medical pressure sensitive adhesives according to claim 1, characterized. that the crosslinking agent is a metal chelate, a metal acid ester, a blocked polyisocyanate, an epoxy, an aziridine or a triazine resin.
7. Medizinische Haftklebstoffe nach Anspruch 1, dadurch gekennzeichnet . daß das Polyol Glyzerin ist.7. Medical pressure sensitive adhesives according to claim 1, characterized. that the polyol is glycerin.
8. Medizinische Pflaster mit guter Haftung auf der Haut, dadurch gekennzeichnet, daß es als die Hauthaftung vermittelnden Kleber einen Haftklebstoff nach einem der Ansprüche 1 bis 7 aufweist.8. Medical plasters with good adhesion to the skin, characterized in that it has a pressure-sensitive adhesive as claimed in one of claims 1 to 7 as the skin-promoting adhesive.
9. Medizinische Pflaster nach Anspruch 8, gekennzeichnet durch textile Flächengebilde, Folien, Schäume oder Papier als Träger.9. Medical plasters according to claim 8, characterized by textile fabrics, foils, foams or paper as a carrier.
10. Medizinisches Pflaster nach Anspruch 8 oder 9, konfektioniert als Wund- bzw. Fixierpflaster.10. Medical plaster according to claim 8 or 9, made up as a wound or fixation plaster.
11. Medizinisches Pflaster nach Anspruch 8, konfektioniert als Occlusivverband für die transdermale Applikation von Wirkstoffen.11. Medical plaster according to claim 8, made up as an occlusive dressing for the transdermal application of active ingredients.
12. Medizinische Haftklebstoffe nach einem der Ansprüche 1-7 , konfektioniert für die Erzeugung von nässeunempfindlichen Occlusivverbänden.12. Medical pressure sensitive adhesives according to one of claims 1-7, made up for the production of moisture-insensitive occlusive dressings.
13. Medizinische Pflaster oder Haftklebstoffe nach einem der vorangehenden Ansprüche in sterilisierter Form. 13. Medical plasters or pressure sensitive adhesives according to one of the preceding claims in sterilized form.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/214,856 US6198017B1 (en) | 1996-07-18 | 1997-06-28 | Medical pressure-sensitive adhesives with high permeability to water vapor and high adhesive force, and plasters provided therewith |
| EP97930438A EP0912203A1 (en) | 1996-07-18 | 1997-06-28 | Medical pressure-sensitive adhesives with high permeability to water vapour and high adhesive force, and plasters provided therewith |
| JP10506479A JP2000516113A (en) | 1996-07-18 | 1997-06-28 | Medicinal pressure-sensitive adhesive having high water vapor permeability and adhesive strength and plaster using the adhesive |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19628999.8 | 1996-07-18 | ||
| DE19628999A DE19628999C1 (en) | 1996-07-18 | 1996-07-18 | Medical pressure sensitive adhesives with high water vapor permeability and adhesive strength and plasters provided with them and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1998003208A1 true WO1998003208A1 (en) | 1998-01-29 |
Family
ID=7800180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1997/003392 WO1998003208A1 (en) | 1996-07-18 | 1997-06-28 | Medical pressure-sensitive adhesives with high permeability to water vapour and high adhesive force, and plasters provided therewith |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6198017B1 (en) |
| EP (1) | EP0912203A1 (en) |
| JP (1) | JP2000516113A (en) |
| CA (1) | CA2260844A1 (en) |
| DE (1) | DE19628999C1 (en) |
| WO (1) | WO1998003208A1 (en) |
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| EP1025823A1 (en) | 1999-02-02 | 2000-08-09 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive attachment means to facilitate water adhesion stability with low pain level removal |
| EP1025867A1 (en) | 1999-02-02 | 2000-08-09 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive flange to facilitate adhesion in oily conditions |
| EP1025824A1 (en) | 1999-02-02 | 2000-08-09 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive flange |
| EP1044667A1 (en) | 1999-04-12 | 2000-10-18 | The Procter & Gamble Company | Container for the collection of bodily waste. |
| US6441092B1 (en) | 1999-06-18 | 2002-08-27 | 3M Innovative Properties Company | Wet-stick adhesives |
| US6518343B1 (en) | 1999-06-18 | 2003-02-11 | 3M Innovative Properties Company | Wet-stick adhesives, articles, and methods |
| US6544642B2 (en) | 1999-02-02 | 2003-04-08 | The Procter & Gamble Company | Disposable absorbent articles with improved adhesive for attachment to the skin to facilitate adhesion in oily conditions |
| US6607516B2 (en) | 1999-02-02 | 2003-08-19 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive flange to facilitate adhesion in oily conditions |
| US6710099B2 (en) | 1999-02-02 | 2004-03-23 | The Procter & Gamble Company | Disposable absorbent articles with improved adhesive for attachment to the skin to facilitate water adhesion stability with low pain level removal |
| US6720387B1 (en) | 1998-02-18 | 2004-04-13 | 3M Innovative Properties Company | Hot-melt adhesive compositions comprising acidic polymer and basic polymer blends |
| US6878756B2 (en) | 1999-02-02 | 2005-04-12 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive flange attachment means to facilitate water adhesion stability with low pain level removal |
| US7232858B2 (en) | 2002-08-14 | 2007-06-19 | The Procter & Gamble Company | Thermoplastic hydrophilic adhesive compositions for attachment on dry and wet surfaces and with increased water adhesion stability |
| WO2010077306A1 (en) | 2008-12-17 | 2010-07-08 | Carlozzi Antonella F | Feminine undergarment |
| US7927703B2 (en) | 2003-04-11 | 2011-04-19 | 3M Innovative Properties Company | Adhesive blends, articles, and methods |
| WO2011120507A1 (en) * | 2010-04-03 | 2011-10-06 | Lohmann Gmbh & Co. Kg | Acrylate adhesive for use on the skin |
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| US6232366B1 (en) * | 1999-06-09 | 2001-05-15 | 3M Innovative Properties Company | Pressure sensitive conductive adhesive having hot-melt properties and biomedical electrodes using same |
| WO2000078885A1 (en) * | 1999-06-18 | 2000-12-28 | 3M Innovative Properties Company | Wet-stick adhesives |
| JP3525876B2 (en) * | 2000-08-23 | 2004-05-10 | 花王株式会社 | Steam generator |
| DE10218570B4 (en) * | 2002-04-26 | 2007-10-18 | Lohmann Gmbh & Co Kg | Acrylate copolymers and PSAs obtainable therefrom for bonding low-energy surfaces and their use |
| DE10251256A1 (en) * | 2002-11-04 | 2004-05-13 | Novosis Ag | Transdermal drug delivery system for oxybutynin |
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| US9017723B2 (en) | 2010-04-30 | 2015-04-28 | Teikoku Pharma Usa, Inc. | Propynylaminoindan transdermal compositions |
| US9119799B2 (en) | 2011-03-24 | 2015-09-01 | Teikoku Pharma Usa, Inc. | Transdermal compositions comprising an active agent layer and an active agent conversion layer |
| US9913812B2 (en) | 2011-11-09 | 2018-03-13 | Teikoku Pharma Usa, Inc. | Methods for the treatment of skin neoplasms |
| JP6050896B2 (en) | 2012-11-02 | 2016-12-21 | テイコク ファーマ ユーエスエー インコーポレーテッド | Propinylaminoindan transdermal composition |
| WO2023042789A1 (en) * | 2021-09-15 | 2023-03-23 | 東洋インキＳｃホールディングス株式会社 | Adhesive composition and adhesive sheet |
| JP7067663B1 (en) | 2021-09-15 | 2022-05-16 | 東洋インキＳｃホールディングス株式会社 | Adhesives and adhesive sheets |
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- 1997-06-28 WO PCT/EP1997/003392 patent/WO1998003208A1/en not_active Application Discontinuation
- 1997-06-28 CA CA002260844A patent/CA2260844A1/en not_active Abandoned
- 1997-06-28 JP JP10506479A patent/JP2000516113A/en not_active Ceased
- 1997-06-28 EP EP97930438A patent/EP0912203A1/en not_active Withdrawn
- 1997-06-28 US US09/214,856 patent/US6198017B1/en not_active Expired - Fee Related
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| WO1984003837A1 (en) * | 1983-04-07 | 1984-10-11 | Minnesota Mining & Mfg | Adhesive and adhesive-coated sheet material for moist skin |
| EP0387751A2 (en) * | 1989-03-15 | 1990-09-19 | Nitto Denko Corporation | Medicated plasters |
| DE4126230A1 (en) * | 1991-08-08 | 1993-02-11 | Lohmann Gmbh & Co Kg | ADHESIVE TAPE |
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|---|---|---|---|---|
| US6800680B2 (en) | 1998-02-18 | 2004-10-05 | 3M Innovative Properties Company | Hot-melt adhesive composition comprising acidic polymer and basic polymer blends |
| US6720387B1 (en) | 1998-02-18 | 2004-04-13 | 3M Innovative Properties Company | Hot-melt adhesive compositions comprising acidic polymer and basic polymer blends |
| EP1025867A1 (en) | 1999-02-02 | 2000-08-09 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive flange to facilitate adhesion in oily conditions |
| EP1025824A1 (en) | 1999-02-02 | 2000-08-09 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive flange |
| US6878756B2 (en) | 1999-02-02 | 2005-04-12 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive flange attachment means to facilitate water adhesion stability with low pain level removal |
| EP1025823A1 (en) | 1999-02-02 | 2000-08-09 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive attachment means to facilitate water adhesion stability with low pain level removal |
| US6544642B2 (en) | 1999-02-02 | 2003-04-08 | The Procter & Gamble Company | Disposable absorbent articles with improved adhesive for attachment to the skin to facilitate adhesion in oily conditions |
| US6607516B2 (en) | 1999-02-02 | 2003-08-19 | The Procter & Gamble Company | Disposable human waste management devices with improved adhesive flange to facilitate adhesion in oily conditions |
| US6710099B2 (en) | 1999-02-02 | 2004-03-23 | The Procter & Gamble Company | Disposable absorbent articles with improved adhesive for attachment to the skin to facilitate water adhesion stability with low pain level removal |
| EP1044667A1 (en) | 1999-04-12 | 2000-10-18 | The Procter & Gamble Company | Container for the collection of bodily waste. |
| US6518343B1 (en) | 1999-06-18 | 2003-02-11 | 3M Innovative Properties Company | Wet-stick adhesives, articles, and methods |
| US6441092B1 (en) | 1999-06-18 | 2002-08-27 | 3M Innovative Properties Company | Wet-stick adhesives |
| US6903151B2 (en) | 1999-06-18 | 2005-06-07 | 3M Innovative Properties Company | Wet-stick adhesives, articles, and methods |
| US7232858B2 (en) | 2002-08-14 | 2007-06-19 | The Procter & Gamble Company | Thermoplastic hydrophilic adhesive compositions for attachment on dry and wet surfaces and with increased water adhesion stability |
| US7927703B2 (en) | 2003-04-11 | 2011-04-19 | 3M Innovative Properties Company | Adhesive blends, articles, and methods |
| WO2010077306A1 (en) | 2008-12-17 | 2010-07-08 | Carlozzi Antonella F | Feminine undergarment |
| WO2011120507A1 (en) * | 2010-04-03 | 2011-10-06 | Lohmann Gmbh & Co. Kg | Acrylate adhesive for use on the skin |
| CN102821792A (en) * | 2010-04-03 | 2012-12-12 | 罗曼两合公司 | Acrylate adhesive for use on the skin |
| KR101757018B1 (en) | 2010-04-03 | 2017-07-12 | 로흐만 게엠베하 운트 캄파니, 카게 | Acrylate adhesive for use on the skin |
| US10034955B2 (en) | 2010-04-03 | 2018-07-31 | Lohmann Gmbh & Co. Kg | Acrylate adhesive for use on the skin |
| US10996645B1 (en) | 2017-04-01 | 2021-05-04 | Smart Power Partners LLC | Modular power adapters and methods of implementing modular power adapters |
Also Published As
| Publication number | Publication date |
|---|---|
| US6198017B1 (en) | 2001-03-06 |
| JP2000516113A (en) | 2000-12-05 |
| CA2260844A1 (en) | 1998-01-29 |
| EP0912203A1 (en) | 1999-05-06 |
| DE19628999C1 (en) | 1998-03-12 |
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